WO2004053019A1 - Organic electroluminescent device material and organic electroluminescent device using same - Google Patents

Abstract

An organic electroluminescent (EL) device material composed of a compound having a specific nitrogen-containing fused ring structure is disclosed. An organic EL device wherein one or more organic thin-film layers are interposed between a cathode and an anode and at least one of the organic thin-film layers contains the organic EL device material is also disclosed. The organic EL device material enables to form a long-life organic EL device which utilizes phosphorescent emission and has a high luminous efficiency. The organic EL device is fabricated using this organic EL device material.

Description

TECHNICAL FIELD The present invention relates to a material for an organic electroluminescence device and an organic electroluminescence device using the same.

 The present invention relates to a material for an organic electroluminescence device and an organic electroluminescence device (organic bright EL device) using the same. In particular, the invention relates to a material for an organic EL device which utilizes phosphorescent light emission and has a high luminous efficiency. It is related to organic EL devices

^ 冃 景. Technology

Organic EL devices are self-luminous devices that use the principle that a fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode when an electric field is applied. Eastman Kodak's CW Tang et al. Report on low-voltage driven organic EL devices using stacked devices (CW Tang, SA Vanslyke, Applied Physics Letters, 51, 913, 1). 1987), organic EL devices using organic materials as constituent materials have been actively researched. Tang and colleagues use tris (8-hydroxyquinolinol aluminum) for the light-emitting layer and a triflenyldiamine derivative for the hole transport layer. The advantages of the stacked structure include: increasing the efficiency of hole injection into the light-emitting layer; increasing the efficiency of exciton generation by blocking electrons injected from the cathode and recombining; Examples include confining excitons. As shown in this example, the element structure of the organic EL element includes a hole transport (injection) layer, a two-layer electron transport / emission layer, or a hole transport (injection) layer, an emission layer, and an electron transport (injection) layer. The three-layer type is well known. In such a stacked structure element, injected holes and electrons In order to increase the recombination efficiency, the device structure and the forming method have been devised.

 As luminescent materials for organic EL devices, luminescent materials such as chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bis (styrylaryl) ylene derivatives, and oxaziazole derivatives are known. Reports that light in the visible region from blue to red can be obtained, and the realization of a color display device is expected (for example, see JP-A-8-239655, In addition, in recent years, organic light emitting materials other than light emitting materials have been used for light emitting layers of organic EL elements in organic EL devices. (Eg, DF O 'Brien and MA Baldo et al "Improved energy transfer in electrophosphorescent devices" Applied Physics lette rs Vol. 74 No. 3, pp442-444, January 18, 1999, MA Baldo et al "Very high-ef f iciencygreen organic 1 ight-emitting devices based on electrophosphorescence "Applied Physics letters Vol. 75 No. 1, pp4-6, July 5, 1999) High luminous efficiency has been achieved by using the singlet state and triplet state of the excited state of the organic EL element. Due to the difference, singlet excitons and triplet excitons are considered to be generated in a ratio of 3: 1. Therefore, using an adjacent light-emitting material is 3 to 4 times that of a device using only fluorescence. Achieving luminous efficiency is considered.

An organic EL device utilizing such adjacent light emission is under study, and a long-life organic EL device having high luminous efficiency is also being studied. As one of them, for example, Japanese Patent Application Laid-Open No. 2002-010476 discloses a light blue light emitting device in which a light emitting layer contains a phosphorescent compound and the external quantum efficiency is 10%. ing. However, Japanese Patent Application Laid-Open No. 2002-100476 describes the luminous efficiency and luminance of the device. It is not known whether or not it has practical performance, and there has been a demand for an organic EL device using neighboring light emission having a practical level of luminous efficiency and lifetime. Disclosure of the invention

 The present invention has been made in order to solve the above-mentioned problems, and has an object to provide a material for an organic EL device having high luminous efficiency using phosphorescent light emission and an organic EL device using the same. I do.

 The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, by using a compound having a specific structure of a nitrogen-containing fused ring structure as a material for an organic EL device, utilizing phosphorescent light emission, The inventors have found that an organic EL device having high luminous efficiency can be obtained, and have solved the present invention.

 That is, the present invention provides a material for an organic electroluminescence device comprising a compound represented by the following general formula (1).

(Wherein, X, to X _a each represent a carbon atom or a nitrogen atom, at least one is a nitrogen atom. If X, either ～Kai ₈ is a carbon atom, bonded to carbon atoms and are R, to R ₈ represents a substituent. in this case, R, to R ₈ in which adjacent is either Itokichi combined and may form a ring. X, to X ₈ each other When R is a nitrogen atom, R and -R ₈ bonded to the nitrogen atom are not shared Represents an electron pair. R ₉ represents a substituent. )

 Further, the present invention provides an organic EL device in which one or more organic thin film layers are sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers contains the organic EL device material. It is intended to provide an organic EL device. Of the organic thin film layers, the light emitting layer, the electron transport layer and / or the electron injection layer, or the hole transport layer and / or the hole injection layer preferably contain the organic EL element material. BEST MODE FOR CARRYING OUT THE INVENTION

 The material for an organic EL device of the present invention comprises a compound represented by the following general formula (1).

X, to X ₈ each represents a carbon atom or a nitrogen atom, at least one is a nitrogen atom. If X, either ～Kai ₈ is a carbon atom, to R ₈ are bonded to the carbon atom, represent a substituent. In this case, adjacent R, to R ₈ may be bonded to each other to form a ring. When any of X and X ₈ is a nitrogen atom, R and R ₈ bonded to the nitrogen atom respectively represent a lone pair. R ₉ represents a substituent.

The substituents represented by R, to R _{3 can} be represented by 1 L or 1 L to Y, respectively, and L is any of X, to X ₈ (in the case of R, to R ₉ ), Or N (for R ₉ ) Directly.

 L is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 10 carbon atoms. Linear or branched alkyl group, substituted or unsubstituted cycloalkyl group having 6 to 40 carbon atoms, substituted or unsubstituted amino group having 2 to 40 carbon atoms, substituted or unsubstituted carbon number of 1 to 4 0 straight-chain or branched alkoxy group, halogen atom, nitro group, or substituted or unsubstituted arylene group having 6 to 40 carbon atoms, substituted or unsubstituted divalent heterocyclic ring having 2 to 40 carbon atoms A substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms; and a substituted or unsubstituted cycloalkylene group having 6 to 40 carbon atoms.

 Y is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 1 0 straight-chain or branched alkyl group, substituted or unsubstituted cycloalkyl group having 6 to 40 carbon atoms, substituted or unsubstituted amino group having 2 to 40 carbon atoms, substituted or unsubstituted carbon number of 1 to 40 40 straight-chain or branched alkoxy groups, halogen atoms or nitro groups.

Examples of the aryl group of L include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, and 2-phenanthryl. Group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthenyl senyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2- Biphenylyl, 3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl, p-nitrophenyl-3-yl, p-phenyl-2-yl Group, m-taphenyl-2-yl group, m-vinyl group 3-yl, m-terphenyl-2-yl group, 0-tolyl group, m-tolyl group, p-tolyl Group, p-t-butylphenyl group, p- (2-phenylpropyl Le) phenyl group, 3-methyl-2- Naphthyl group, 4-methyl-11-naphthyl group, 4-methyl-1-anthryl group, 4-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, fluorenyl group, perfluoroaryl group No.

 Examples of the heterocyclic group represented by L include pyrrole, pyridine, pyrimidine, pyrazine, aziridine, azazidine, indlizine, imidazole, indole, isoindole, indazole, purine, pteridine, j3-carboline and the like.

Examples of the alkyl group of L include a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and an n-pentyl group , N-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl Group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group 1,2-dichloroethyl, 1,3-dichloroethyl, 1,3-dichloro-1,2-butyl, 1,2,3-trichloropropyl, bromomethyl , 1_bu Lomoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibutyl moisop pill group, 2,3-dibutyl mo-butyl group, 1,2,3- Tribromopropyl group, lodomethyl group, 1-lodoethyl group, 2-lodoethyl group, 2-lodoisobutyl group, 1,2-jodoethyl group, 1,3-jodoethyl group, 2, 3-jodo-t-butyl group, 1,2,3-tolypropylpropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2- Diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diaminot-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2 —Cyanisobutyl group, 1,2-disi Anoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2 _Nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t_butyl group, 1, I, 3-trinitropropyl group and the like.

 Further, as the substituted aryl group, for example, when a phenyl group having 6 carbon atoms is substituted with a substituent of a phenyl group or a methyl group, the following structures are exemplified.

Examples of the cycloalkyl group of L include a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl, an adamantyl group, a norbornyl group, and the like.

 Examples of the amino group represented by L include a dimethylamino group, a methylethylamino group, a diphenylamino group, a diisopropylamino group, a bis-diphenylamino group, a carbazolyl group, a getylamino group, a ditolylamino group, an indolyl group, and a pyridinyl group. And a pyrrolidinyl group.

Alkoxy groups of the L is a group represented by a OY ^1, examples of Y ¹ include a methyl group, triflate Ruo Russia methyl group, Echiru group, a propyl group, an isopropyl radical, n one-butyl group, s- Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyxethyl, 2-hydroxyethyl, 2 —Hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, methyl group, 1, —Chloroethyl group, 2-Chloroethyl group, 2-Chloroisobutyl group 1,1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloromethylpropyl, bromomethyl, 1-bromoethyl, 2-bromo Diethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo_t-butyl group, 1,2,3-tribromopropyl group, Methyl, 1-ethyl, 2-ethyl, 2-isobutyl, 1,2-jodoethyl, 1,3-iodoisopropyl, 2,3-jodo-t-butyl , 1,2,3-triodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-dia Minoisopropyl group, 2,3-diamino-t-butyl group, 1 , 2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyanot- Butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1,2-troethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, Examples include a 2,3-dinitrate mono-t-butyl group and a 1,1,3-trinitropropyl group.

 Examples of the halogen atom for L include fluorine, chlorine, bromine, iodine and the like.

 Examples of the arylene group of L include those obtained by converting the example of the aryl group to a divalent group.

 Further, as the substituted aryl group, for example, when a phenylene group having 6 carbon atoms is substituted with a substituent of a phenyl group or a methyl group, the following structures are exemplified.

Examples of the divalent substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms of L include those obtained by converting the above examples of the heterocyclic group into divalent groups.

 Examples of the alkylene group for L include those in which the examples of the alkyl group are divalent groups.

 Examples of the cycloalkyl group of L include those in which the examples of the cycloalkyl group are divalent groups.

 Examples of the aryl group, the heterocyclic group, the alkyl group, the cycloalkyl group, the amino group, the alkoxy group, and the halogen atom represented by Y include the same as those described above for L.

In the compound represented by the general formula (1), it is preferable that 1 to 3 of X, to X ₈ are nitrogen atoms and the remainder is a carbon atom, and Χ ₃ and / or Χ ₆ are nitrogen atoms. More preferably, they are atoms, and the remainder are carbon atoms.

Also, previous remarks himself R, at least one of to R _8, an carbolinyl group, ie, the L and / or Y is further preferably one carbolinyl group. Wherein X, to X ₈ and R, is a group that substitutes a hydrogen atom of the substituent represented by to R _9, respectively, a halogen atom (fluorine, chlorine, bromine, etc.), Shiano group, a silyl group, an amino group And an aryl group, an aryloxy group, a heterocyclic group, an alkyl group, an alkoxy group, an aralkyl group, or a cycloalkyl group.

Specific examples of the material for an organic EL device represented by the general formula (1) of the present invention are shown below, but it should not be construed that the invention is limited thereto.

L8Sl0 / £ 00ZdT / 13d 6I0 £ 00Z OAV

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L8SlO / £ OOZdT / 13d 6I0 £ OOZ OAV The material for an organic EL device comprising the compound represented by the general formula (1) in the present invention has a triplet energy gap of 2.5 to 3.3 eV, and a triplet energy gap of 2.6 to 3.2 eV. It is preferred that there is.

 The material for an organic EL device comprising the compound represented by the general formula (1) in the present invention has a singlet energy gap of 2.8 to 3.8 eV, and a singlet energy gap of 2.9 to 3.6 eV. It is preferred that there is.

 The organic EL device of the present invention is an organic EL device in which one or more organic thin film layers are sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is represented by the general formula (1). Contains a material for organic EL devices consisting of compounds.

 In addition, the organic EL device of the present invention is an organic EL device comprising the compound of the general formula (1) in a light emitting layer, an electron transport layer and / or an electron injection layer, or a hole transport layer and / or a hole injection layer. It is preferable to contain an element material.

 In the organic EL device of the present invention, the organic thin film layer preferably contains a phosphorescent compound. As the phosphorescent compound, a metal complex or the like which emits light by triplet excitation or higher multiplet excitation is preferable. For example, the following examples are given.

 (K-1) (K-2) (K-3)

(-4) (-5) (-6)

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in-yi) (ε ι

(-) (14-) (0! ■-!)

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 (8-¾)

L8Sl0 / £ 00ZdT / 13d 6ΐοε 00Z OAV The material for an organic EL device of the present invention is preferably a host material for an organic EL device. The host material is capable of injecting holes and electrons, has a function of transporting holes and electrons, and has a function of emitting fluorescence by recombination.

 The compound of the general formula (1) according to the present invention has a singlet energy gap as high as 2.8 to 3.8 eV, and a triplet energy gap as 2.5 to 3.3 eV. Since it is high, it is also useful as an organic host material for a phosphorescent device.

 Here, a phosphorescent element is a substance whose emission intensity based on a transition from a triplet energy state to a ground singlet state is higher than that of another substance. It refers to an organic electroluminescent device using so-called phosphorescence, which includes a phosphorescent material such as an organometallic complex containing at least one metal selected from Groups 1 to 11.

 In the light-emitting layer of an organic EL device, the generated molecular excitons are a mixture of singlet excitons and triplet excitons, and singlet excitons and triplet excitons are generally It is said that more triplet excitons are generated in a ratio of 1: 3. In an organic EL device using ordinary fluorescence, excitons that contribute to light emission are singlet excitons, and triplet excitons are non-emissive. As a result, the triplet excitons are eventually consumed as heat, and light is emitted from the singlet excitons with a low generation rate. Therefore, in the organic EL device, of the energy generated by the recombination of holes and electrons, the energy transferred to the triplet exciton is a large loss.

For this reason, by using the compound of the present invention for a phosphorescent device, the energy of triplet excitons can be used for light emission, so that it is considered that three times the luminous efficiency of the device using fluorescence can be obtained. Further, when the compound of the present invention is used for a light-emitting layer of a phosphorescent element, the compound has an energy higher than the excited triplet level of a photoluminescent organometallic complex containing a metal selected from Groups 7 to 11 contained in the layer. Excited state Has triplet level, provides more stable thin film shape, has high glass transition temperature (Tg: 80-160 ° C), and efficiently holes and / or electrons Can be transported, electrochemically and chemically stable, Trough. It is considered that impurities that cause quenching or quenching of light emission are unlikely to occur during manufacturing or use.

 The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between the anode and the cathode as described above. In the case of a single layer type, a light emitting layer is provided between an anode and a cathode. The light-emitting layer contains a light-emitting material and may further contain a hole-injection material or an electron-injection material for transporting holes injected from an anode or electrons injected from a cathode to the light-emitting material. . Further, it is preferable that the light emitting material has extremely high fluorescence quantum efficiency, high hole transport ability and electron transport ability, and forms a uniform thin film. Examples of the multilayer organic EL device include (anode / hole transport layer / light emitting layer / cathode), (anode / light emitting layer / electron transport layer / cathode), (anode / hole transport layer / light emitting layer / electron transport layer). (Cathode).

 In the light emitting layer, if necessary, in addition to the compound of the general formula (1) of the present invention, further known host materials, light emitting materials, doping materials, hole transporting materials and electron transporting materials may be used and used in combination. You can also. The organic EL device has a multi-layer structure, which can prevent reduction in brightness and life due to quenching.Other doping materials can improve light emission brightness and luminous efficiency, and other doping that contributes to phosphorescence. When used in combination with a material, conventional light emission luminance and light emission efficiency can be improved.

Further, the hole transporting layer, the light emitting layer, and the electron transporting layer in the organic EL device of the present invention may each be formed in a layer configuration of two or more layers. In this case, in the case of a hole transport layer, a layer that injects holes from the electrode is called a hole injection layer, and a layer that receives holes from the hole injection layer and transports holes to the light emitting layer is called a hole transport layer. Similarly, in the case of an electron transport layer, a layer that injects electrons from the electrode is called an electron injection layer, and a layer that receives electrons from the electron transport layer and transports electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic thin film layer or metal electrode. In the organic EL device of the present invention, the electron transport layer / the hole transport layer may contain the organic EL device material of the present invention comprising the compound represented by the general formula (1). The layer and the hole blocking layer may contain the material for an organic EL device of the present invention, and the phosphorescent compound and the material for an organic EL device of the present invention may be used as a mixture.

 Examples of the luminescent material or the host material that can be used in the organic thin film layer together with the compound of the general formula (1) of the present invention include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthalene perylene, and naphthalene. Perylene, lidone perinone, lidone perinone, naphthalene perinone, diphenylbutanediene, tetraphenylbutadiene, coumarin, oxaziazolyl, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentagen, quinoline metal complex, Aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminoanthracene, diaminoforce rubazole, virane, thiovirane, polymethine, merocyanine, imida Examples include, but are not limited to, cheloxylated oxinoide compounds, quinacridone, rubrene, stilbene derivatives, and fluorescent dyes.

The hole injecting material has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injecting effect on the light emitting layer or the light emitting material, and has a function of exciters generated in the light emitting layer. A compound that prevents migration to an electron injection layer or an electron injection material and has excellent ability to form a thin film is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazoles, oxaziazoles, triazoles, imidazoles, imidazolones, imidazolylthiones, pyrazolines, pyrazolones, tetrahydroimidazols, oxazoles, oxazirazols, hydrazones, hydrazones. Arylalkane, stilbene, butadiene, benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymer But are not limited to these Absent.

 Among these hole injection materials, more effective hole injection materials are aromatic tertiary amine derivatives or phthalocyanine derivatives. Specific examples of the aromatic tertiary amamine derivative include triphenylamine, tritolylamine, tolyldiphenylamine,

N, N, diphenyl-1-N, N '-(3-methylphenyl) -11,1-biphenyl_4,4'diamine, N, N, N', N '-(4-methylphenyl) 1-1,1,1, one Phenyl 4, 4 'Jiamin, N, N, N', N '— (4-Methylphenyl) — 1, 4-biphenyl-1, 4, Jiamin, N, N' Jiphenyl 1 N, N, 1 Dinaphthyl 1 1 , Γ — biphenyl 2,4 'diamine, N, N, 1 (methylphenyl) 1 N, N' 1 (4 1 n-butylphenyl) — phenanthrene 1 9,10-diamine, N, N—bis (4 —Di-4-tolylaminophenyl) —4-phenyl-cyclohexane and the like, or an oligomer or polymer having an aromatic tertiary amine skeleton, but is not limited thereto. Specific examples of the phthalocyanine (Pc) _{derivative, H 2 Pc, CuPc, CoPc} , N i Pc, ZnPc, PdPc, FePc, MnPc, C l Al Pc, C l GaP c, C l I nPc, C l SnPc, C phthalocyanine derivatives and naphthalocyanine derivatives such as l ₂ S i Pc, (H〇) Al Pc, (HO) GaPc, VOPc, T i〇Pc, MoOPc, GaPc-0-GaPc. It is not limited.

The electron injecting material has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injecting effect on the light emitting layer or the light emitting material, and has the hole injecting layer of exciters generated in the light emitting layer Compounds that prevent migration to the surface and have excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiovirandoxide, oxazole, oxazine diazole, triazole, imidazole, perylenetetracarboxylic acid, quinoxaline, fluorenylidene methane, anthraquinodimethane, anthrone, etc. And their derivatives. It is not limited.

 Among these electron injecting materials, more effective electron injecting materials are metal complex compounds or nitrogen-containing five-membered ring derivatives. Specific examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolina) aluminum, tris (2-methyl_8-hydroxyquinolina) aluminum, tris (8-hydroxyquinolina) gallium, bis (10-hydroxybenzo [h] quinolina 1) Beryllium, bis (10-hydroxybenzo [h] quinolinate) zinc, bis (2-methyl-18-quinolinate) gallium chloride, bis (2-methyl-8-quinolinate)

(0-cresolate) gallium, bis (2-methyl-18-quinolinato) (11-naphtholate) aluminum, bis (2-methyl-18-quinolinato) (2-naphtholate) gallium However, it is not limited to these. The nitrogen-containing five-membered derivative is preferably an oxazole, thiazole, oxaziazole, thiadiazole or triazole derivative. Specifically, 2,5-bis (1-phenyl) 1-1,3,4-xazole, dimethyl POP OP, 2,5-bis (1-phenyl) -1,3,4-thiazol, 2,5-bis (1-phenyl) — 1,3,4-oxaziazol, 2- (4,1-tert-butylphenyl) -5— (4 "—biphenyl) 1,3,4— Oxaziazol, 2, 5-bis

(1-naphthyl) 1, 1, 3, 4-oxaziazole, 1, 4-bis [2_ (5-phenyloxaxazolyl)] benzene, 1, 4-bis [2-(5-phenylo) 1- (4'-tert-butylphenyl) -1-5- (4 "-biphenyl) 1-1,3,4-thiadiazole, 2,5-bis (1-naphthyl) -1 1,3,4-thiadiazol, 1,4-bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4,1-tert-butylbutyl) 1-5- (4 ,, 1 biphenyl) 1,3,4_triazole, 1,5 —Bis (1-naphthyl) _1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene, etc., but not limited thereto .

 The charge injecting property can be improved by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.

 As the conductive material used for the anode of the organic EL device of the present invention, those having a work function of more than 4 eV are suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver , Gold, platinum, palladium and their alloys; metal oxides such as tin oxide and indium oxide used for ITO and NESA substrates; and organic conductive resins such as polythiophene-polypyrrole. As the conductive material used for the cathode, those having a work function of less than 4 eV are suitable, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, and the like. These alloys are used, but are not limited to these. Representative examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature, atmosphere, degree of vacuum, and the like of the evaporation source, and is selected as an appropriate ratio. The anode and the cathode may be formed of two or more layers if necessary.

The organic EL device of the present invention may have an inorganic compound layer between at least one of the electrodes and the organic thin film layer. Preferred inorganic compounds used for the inorganic compound layer include alkali metal oxides. things, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, S i Ox, A 1 〇 _{x, S i Nx, S i} ON, A 1 ON, G e 〇 _x, L i 〇 _x, L i _{〇_N, T i O x, T i} ON, T a O x, T A_〇_N, T a N _x, C and various oxides, nitrides, oxide nitrides In particular, as components of the layer in contact with the anode, Siox, A1〇, SiNx, SiON, A1ON, GeOx, and C form a stable injection interface layer. Preferred. As the components of the layer, in particular in contact with the cathode, L i F, M g F 2, C a F 2, M g F 2, N a F are preferred.

 It is desirable that at least one surface of the organic EL device of the present invention is sufficiently transparent in an emission wavelength region of the device in order to efficiently emit light. It is also desirable that the substrate is transparent.

 The transparent electrode is set so as to secure a predetermined translucency by a method such as vapor deposition or sputtering using the above conductive material. It is desirable that the electrode on the light emitting surface has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strengths and has transparency, and examples thereof include a glass substrate and a transparent resin film. Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polychlorinated vinyl, polybutyl alcohol, polyvinyl butyral, and nylon. , Polyetheretherketone, Polysulfone, Polyethersulfone, Tetrafluoroethylene-perfluoroalkylvinylether copolymer, Polyvinylfluoride, Tetrafluoroethylene-ethylene copolymer Coalescence, Tetrafluoroethylene-hexafluoropropylene copolymer, Polychlorinated trifluoroethylene, Polyvinylidene fluoride, Polyester, Polycarbonate, Polyurethane, Polyimide, Polyetherimide, Polyimide Polypropylene.

 In the organic EL device of the present invention, a protective layer can be provided on the surface of the device, or the entire device can be protected with silicon oil, resin, or the like, in order to improve stability against temperature, humidity, atmosphere, and the like.

Each layer of the organic EL device of the present invention may be formed by any of dry film forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, dating, and flow coating. Can be. The thickness of each layer is not particularly limited, but needs to be set to an appropriate thickness. If the film thickness is too large, a large applied voltage is required to obtain a constant light output, and the luminous efficiency deteriorates. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 m, but is more preferably in the range of 10 nm to 0.2 m.

 In the case of the wet film formation method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film. Good. In any of the layers, an appropriate resin or additive may be used to improve film forming properties, prevent pinholes in the film, and the like. Resins that can be used include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethylmethacrylate, polymethylatalylate, and cellulose, and copolymers thereof, and polyisomers. Examples include photoconductive resins such as N-vinylcarbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer. i '

 As described above, by using the material for an organic EL device comprising the compound of the general formula (1) of the present invention in the organic thin film layer of the organic EL device, the organic EL device having high color purity and emitting blue light can be obtained. This organic EL element can be used as, for example, an electrophotographic photosensitive member, a flat light-emitting member such as a flat panel display for a wall-mounted television, a copier, a printer, a backlight of a liquid crystal display, or a light source such as an instrument. It is suitably used for, for example, display boards, marker lights, and accessories. Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

 The triplet energy and singlet energy of the compound were measured as follows.

(1) Measurement of triplet energy The lowest excited triplet energy level Tl was measured. That is, the light spectrum adjacent to the sample was measured (l Owmol / liter EPA (getyl ether: isopentane: ethanol = 5: 5: 2 volume ratio) solution, 77K, quartz cell, 3-8A LUOROLOGII), a tangent was drawn to the rise on the short wavelength side of the adjacent light spectrum, and the wavelength (light emitting end) at the intersection with the horizontal axis was determined. This wavelength was converted to an energy value.

 (2) Measurement of singlet energy (energy gap)

Excitation Singlet energy values were measured. That is, a toluene solution of the sample - the absorbance was measured scan Bae spectrum using Hitachi UV-visible absorption analyzer using (1 0 ⁵ mol / liters). A tangent was drawn to the rise on the long wavelength side of the spectrum, and the wavelength (absorption edge) at the intersection with the horizontal axis was determined. This wavelength was converted to an energy value.

Synthesis Example 1 (Synthesis of Compound (1))

 The synthetic route of compound (1) is shown below.

 (1)

(1) Synthesis of synthetic intermediate (A)

 4 15.0 g (81 mraol) of bromobenzaldehyde and 9.7 g (81 ol) of acetophenone were dissolved in 300 ml of ethanol, and 16.6 ml (8kiraoI) of a 28% sodium methoxide methanol solution was added, followed by stirring at room temperature for 9 hours. After the completion of the reaction, the precipitated crystals were filtered and washed with ethanol to obtain 19.6 g (yield 84%) of a synthetic intermediate (A).

 (2) Synthesis of synthetic intermediate (B)

Synthetic intermediate (A) 9. Og (31mraol), 1-Panacilpyridinium bromide 8.7e (31 brain 1), 19.3 g (250 mmol) of ammonium acetate was suspended in 27 mU of acetic acid, and the mixture was heated under reflux for 12 hours. The reaction solution was cooled to room temperature, toluene and water were added thereto, and after separating into two layers, the organic layer was washed successively with a 10% aqueous sodium hydroxide solution and a saturated saline solution, and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, 27 ml of ethanol was added, and the precipitated crystals were filtered and washed with ethanol to obtain 10.6 g (yield: 88%) of a synthetic intermediate (B). (3) Synthesis of compound (1)

 Synthetic intermediate (B) 3.0 g (8 mmol), —carboline 1.4 g (8 mraol), tris (dibenzylideneacetone) dipalladium 0.18 g (0.2 imol), 2-dicyclohexylphosphino-1,2, I (N, N-dimethylamino) biphenyl 0.23 g (0.6 reference ol), sodium tert-butoxide 1. Og (l mmol) is suspended in 15 ml of toluene, and heated under an argon atmosphere for 20 hours under reflux. did. The reaction solution was cooled to room temperature, and methylene chloride and water were added. After separating into two layers, the mixture was washed with water and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, the residue was purified by silica gel gel chromatography to obtain 1.7 g of crystals (yield 46%).

 The obtained crystal was confirmed to be the target compound by 90 MHz 'Η-NMR and FD-MS (field desorption mass spectrum). The FD-MS measurement results are shown below.

FD-S, calcd for C ₃ = 473, found, ra / z = 473 (M ⁺ , 100)

Synthesis Example 1 (Synthesis of Compound (2))

 The synthetic route of compound (2) is shown below.

(1) Synthesis of synthetic intermediate (C)

 Synthetic intermediate (A) 10. Og (35 mmol) and benzamidine hydrochloride 5.5 g (35 mmol) were suspended in 75 ml of ethanol, 2.8 g (70 mraol) of sodium hydroxide was added, and the mixture was heated under reflux for 18 hours. The reaction solution was cooled to room temperature, 50 ml of water was added, and the mixture was stirred for i hours. The precipitated crystal was filtered and washed with ethanol to obtain 8.2 g of a synthetic intermediate (C) (yield: 61%). (2) Synthesis of compound (2)

 Compound (2) was obtained in the same manner as in Synthesis Example 1 except that the synthetic intermediate (C) was used instead of the synthetic intermediate (B) to obtain 1.8 g of crystals (yield: 45%). Was. The obtained crystal was confirmed to be the target compound by 90 MHz 'Η-NMR and FD-MS. The measurement results of FD-MS are shown below.

FD-MS, calcd for C ₃₃ H ₂₂ N ₄ = 474, found, ra / z = 474 (M ⁺ , 100)

Synthesis Example 3 (Synthesis of Compound (61))

 The synthetic route of the compound (61) is shown below.

 (1) Synthesis of synthetic intermediate (D)

4-bromoiodobenzene 25.4g (90mmol), —Carboline 10. lg (60imol), Tris (dibenzylideneacetone) dipalladium 0.55g (0.6rnmol), 2-dicyclohexylphosphino 2 ′ — (N, N— Dimethylamino) biphenyl 0.71 g (1.8 ramol) and sodium tert-butoxide 8. lg (84 mraoI) were suspended in toluene (60 ml), and the mixture was heated to reflux under an argon atmosphere for 20 hours. Cool the reaction solution to room temperature, add water After separating the two layers, the mixture was washed with water and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain 11.4 g of crystals (yield: 59%).

 (2) Synthesis of synthetic intermediate (E)

 Synthetic intermediate (D) 8. Dissolve lg (25 mmol) in 50 ral toluene and 50 ml of ether, add 21 ml of normal butyllithium hexane solution (1.6 M) (32 Mol) at -40 ° C under argon atmosphere, and add -40 The mixture was stirred at 0 ° C to 0 ° C for 1 hour. Next, the reaction solution was cooled to -70 ° C, a solution obtained by diluting 17 ml (74%) of triisopropyl borate in 25 ml of ether was added dropwise, and the mixture was stirred at -70 ° C for 1 hour, and then cooled to room temperature. The mixture was heated and stirred for 6 hours. Further, 70 ml of 5% hydrochloric acid was added dropwise to the reaction solution, and the mixture was stirred at room temperature for 45 minutes. After separating the reaction solution into two layers, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure to about 1/5, the precipitated crystals were filtered, washed with a mixed solvent of toluene-normalxane and normal hexane in that order, and 3.2 g of synthetic intermediate (E) (yield 45 %).

 (3) Synthesis of compound (61)

 Synthetic intermediate (C) 2.7 g (6.9 t ol), synthetic intermediate (E) 2.0 g (6.9 raraol), tetrakis (triphenylphosphine) palladium 0.16 g (0.14 minol) Γ, 2-dimethoxetane 21 ml And a solution prepared by dissolving 2.2 g (21 marl ol) of sodium carbonate in 11 ml of water was added thereto, and the mixture was refluxed for 9 hours. After separating the reaction solution into two layers, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, 12 ml of ethyl acetate was added, and the precipitated crystals were filtered and washed with ethyl acetate to obtain 2.7 g of crystals (yield: 72%).

 The obtained crystals were confirmed to be the target compound by 90 MHz-NMR and FD-MS. The measurement results of FD-MS are shown below.

FD-MS, calcd for C ₃₉ H 550, found, ra / z = 550 (M +, 100)

Synthesis Example 4 (Synthesis of Compound (68)) The synthetic route of compound (68) is shown below.

 Toluene (F) DMF (G)

 (68)

(1) Synthesis of synthetic intermediate (F)

 4-aminoviridine 7.9 g (8 mol), 2-bromoiodobenzene 25.0 g (88 mmol), tris (dibenzylideneacetone) dipalladium 1.5 g (L6 ol), 1,1,1-bis (diphenylphosphino) 1.8 g (3.2 mmol) of cene and 11.3 g (118 mmol) of sodium tert-butoxide were suspended in 210 ml of toluene, and the mixture was heated and refluxed under an argon atmosphere for 19 hours. The reaction solution was cooled to room temperature, water was added, and two layers were separated, washed with water and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, 50ral of ethanol was added, and the precipitated crystals were filtered and washed with ethanol to obtain 20.5 g (yield 98%) of a synthetic intermediate (F).

 (2) Synthesis of synthetic intermediate (G)

Synthetic intermediate (F) 10.0 g (40 mraol), 0.90 g (4.0 mmol) of palladium acetate, and 5.9 g (56 iranol) of sodium carbonate were suspended in 80 ml of N, N-dimethylformamide, and the suspension was stirred under an argon atmosphere. Reflux with heating for hours. Cool the reaction solution to room temperature, add ethyl acetate and water. Then, after separating into two layers, the mixture was washed with water and saturated saline in this order, and dried with anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, the crystals recrystallized from toluene were separated by filtration and washed with toluene to obtain 4.4 g of a synthetic intermediate (G) (yield 66%).

 (3) Synthesis of synthetic intermediate (H)

 2,4'-Jib mouth moacetophenone 15.0 g (54 olol), 2-aminoviridine 5.2 g (55 麵 ol) were suspended in ethanol 100 ml, sodium hydrogencarbonate 7. Og (83 mraol) was added, and the mixture was heated under reflux for 9 hours. did. The reaction solution was cooled to room temperature, and the precipitated crystals were filtered and washed sequentially with water and ethanol to obtain 12.5 g of a synthetic intermediate (H) (yield: 85%).

(4) Synthesis of compound (68)

 Compound (68) was prepared in the same manner as in Synthesis Example 1 (3) except that synthetic intermediate (H) was used instead of synthetic intermediate (B), and synthetic intermediate (G) was used instead of β-carboline. By performing the same operation, 8 g of crystal L (yield 49%) was obtained.

 The obtained crystal was confirmed to be the target compound by 90 MHz 'Η-NMR and FD-MS. The results of FD-MS measurement are shown below.

FD-MS, calcd for C ₂₄ H, ₆ N ₄ = 360, found, m / z = 360 (M ⁺ , 100)

 Synthesis Example 5 (Synthesis of Compound (72))

 The synthetic route of compound (72) is shown below.

(1) Synthesis of synthetic intermediate (I)

4-Promophenylhydrazine hydrochloride 5. Og (22 ol), sodium hydrogen carbonate 1.9 g (22 ol) was suspended in 100 ml of ethanol, stirred for 1 hour, 5.0 g (22 ol) of dibenzilmeine was added, and the mixture was heated under reflux for 8 hours. Next, 2 ml of concentrated hydrochloric acid (23 marl ol) was added, and the mixture was heated under reflux for 12 hours. The reaction solution was cooled to room temperature, and 2.3 ml (23 mraol) of 30% aqueous sodium hydroxide and 50 ml of water were added. The mixture was stirred for 1 hour, and the precipitated crystals were filtered, washed with ethanol, and synthesized intermediate (L) 7.6 g (quantitative yield) was obtained.

 (2) Synthesis of compound (72)

 Compound (72) was prepared in the same manner as in (3) of Synthesis Example 1 except that synthetic intermediate (I) was used instead of synthetic intermediate (B) to obtain 1.8 g of crystals (yield). Rate 46%).

 The obtained crystals were confirmed to be the target compound by 90 MHz 'H-NMR and FD-MS. The results of FD-MS measurement are shown below.

FD-MS, calcd for C ₃₂ H ₂₂ N ₄ = 462, found, m / z-462 (M +, 100)

Synthesis Example 6 (Synthesis of Compound (2 3))

 The synthesis route of compound (23) is shown below.

Synthesis intermediate (J) synthesized in the same manner as in Synthesis Examples (1) and (2) except that 3,5-dibromobenzaldehyde was used in place of 4-bromobenzaldehyde in (1) of Synthesis Example 1 above. ) 2.5 g (5 mmol), ^ -carboline 1.0 g (6 mmol), tris (dibenzylideneacetone) dipalladium 0.18 g (0.2 country ol), 2-dicyclohexyl phosphinol 2,-(N, N-dimethylamino) biphenyl 0.23 g (0.6imnol), sodium tert-butoxide LOg (llmmol) in 15 ml of toluene Under an atmosphere, the mixture was heated under reflux for 20 hours. The reaction solution was cooled to room temperature, methylene chloride and water were added, and the mixture was separated into two layers, washed with water and dried over anhydrous sodium sulfate. After the organic solvent was distilled off under reduced pressure, the distillation residue was suspended in 15 ml of toluene, and 0.18 g (0.2 mmol) of tris (dibenzylidene aceton) dipalladium, 2-dicyclohexylphosphino 2 ′-(N, N —Dimethylamino) biphenyl (0.23 g, 0.6 mmol) and sodium tert-butoxide (1.0 g, ll-ol) were added, and the mixture was heated to reflux under an argon atmosphere for 20 hours. The reaction solution was cooled to room temperature, methylene chloride and water were added, and the mixture was separated into two layers, washed with water, and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain crystal L7g (yield 53%).

 The obtained crystals were confirmed to be the target compound by 90 MHz 'H-NMR and FD-MS. The results of FD-MS measurement are shown below.

FD-MS, calcd for C ₄₅ H ₂₉ N ₅ = 639, found, m / z = 639 (M ⁺ , 100)

Example 1 (manufacture of organic EL device)

A 25 mm × 75 mm × 0.7 mm thick glass substrate with an ITO transparent electrode (manufactured by Geomatic) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. The glass substrate with the transparent electrode after cleaning is mounted on a substrate holder of a vacuum evaporation apparatus. First, the following copper having a film thickness of 10 nm is coated on the surface where the transparent electrode is formed so as to cover the transparent electrode. A phthalocyanine film (hereinafter abbreviated as “CuPc film”) was formed. This CuPc film functions as a hole injection layer. The following 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl film (hereinafter abbreviated as "a-NPD film") having a thickness of 3 Onm is formed on this CuPc film. did. This α-NPD film functions as a hole transport layer. Further, the compound (1) having a thickness of 30 nm was deposited as a host material on the α-NPD film to form a light emitting layer. At the same time, the following tris (2-phenylpyridine) Ir (hereinafter abbreviated as “I r (ppy) ₃ ”) was added as a phosphorescent Ir metal complex dopant. The concentration of I r (ppy) 3 in the light emitting layer was 5 wt _^0/0. This membrane Functions as a light emitting layer. On this film, the following (1, 下 記 -bisphenyl) -14-olato) bis (2-methyl-8-quino.linoleate) aluminum (hereinafter abbreviated as “BA1q film”) with a thickness of 10 nm ) Was deposited. This BA1q film functions as a hole barrier layer. Further, an aluminum complex of the following 8-hydroxyquinoline (hereinafter abbreviated as “A1q film”) having a thickness of 40 nm was formed on this film. This A 1 Q film functions as an electron injection layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.1 nm, and then aluminum was deposited to a thickness of 150 nm. This A 1 / L i F acts as a cathode. Thus, an organic EL device was manufactured.

 Table 1 shows the results obtained by measuring the triplet energy and singlet energy of the host material used in the light emitting layer by the above-mentioned measuring methods (1) and (2).

 This device was subjected to a conduction test to find that the voltage was 5.2 V and the current density was 0.

At 26 mA / cm ² , a green emission of 99 cd / m ² was obtained, and the chromaticity coordinates were (0.

32, 0.62), the efficiency was 38.6 cd / A. Table 1 shows these results.

ir (ppy) 3 Examples 1 and 3

 An organic EL device was prepared in the same manner as in Example 1 except that the compounds shown in Table 1 were used instead of the compound (1). Similarly, triplet energy and singlet energy, voltage, and current density were similarly measured. Table 1 shows the results of measuring the luminance, luminous efficiency, and chromaticity. Comparative Example 1

 An organic EL device was prepared in the same manner as in Example 1 except that the following compound '(BCz) was used instead of the compound (1), and a triplet energy, a singlet energy, a voltage Table 1 shows the results of measuring the current density, luminance, luminous efficiency, and chromaticity.

Comparative Example 2

 Example 1 was repeated in the same manner as in Example 1 except that the following compound (A-10) described in U.S. Patent Publication No. 2002-283329 was used in place of compound (1). An EL device was manufactured, and the characteristics were evaluated in the same manner as in Example 1. Table 1 shows the results.

A-10 Emitting layer 3

 Current density Luminance Luminous efficiency Chromaticity coordinates

 Nerqui's host

Emission color Material (eV) (eV) (V) (mA / cm ² ) (cd / m ² ) (cd / A) (x, y)

Example 1 (1) 2.8 3.4 5.2 0.26 99 38.6 (0.32,0.62) Green Example 2 (61) 2.6 3.3 5.5 0.24 102 42.8 (0.32,0.61) Green Example 3 (68) 2.7 3.5 5.6 0.27 100 37.2 (0.32 , 0.61) Green Comparative Example 1 (BCz) 2.8 3.6 5.4 0.31 101 32.6 (0.32,0.61) Green Comparative Example 2 (A-10) 3.1 3.7 5.9 0.32 100 31.8 (0.32,0.61) Green As shown in Table 1, Compared with the conventionally known compounds (BCz, A-10) of Comparative Examples 1 and 1, the organic EL device using the material for an organic EL device of the present invention can provide highly efficient green light emission. Further, since the material for an organic EL device of the present invention has a wide energy gap, light-emitting molecules having a wide energy gap can be mixed into a light-emitting layer to emit light.

Example 4

 A 5 mm × 75 mm × 0.7 mm thick glass substrate with an ITO transparent electrode (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The washed glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum evaporation apparatus. First, the transparent electrode is formed on the surface on the side where the transparent electrode is formed so as to cover the transparent electrode. (The film was formed. This CuPc film functions as a hole injection layer. Next, the following 3 nm thick film is formed on the CuPc film.

A 1,1,1-bis [4-N, N-di (paratolyl) aminophenyl] cyclohexane film (hereinafter abbreviated as “TPAC film”) was formed. This TPAC membrane functions as a hole transport layer. Further, the compound (1) having a thickness of 3 O nm was deposited on the TPAC film to form a light emitting layer. At the same time, Ir bis [

(4,6-difluorophenyl) -pyridinato N, C ² '] picolinate (hereinafter abbreviated as "FI rpic") was added. The concentration of FI rpic in the light emitting layer was 7% by weight. This film functions as a light emitting layer. An A1q film having a thickness of 3 O nm was formed on this film. This A 1 q film functions as an electron injection layer. this Thereafter, an alkali metal halide, LiF, was deposited to a thickness of 0.2 nm, and then aluminum was deposited to a thickness of 150 nm. This A 1 / L i F acts as a cathode. Thus, an organic EL device was produced.

 Table 1 shows the results obtained by measuring the triplet energy and singlet energy of the host material used in the light emitting layer by the above-mentioned measuring methods (1) and (2).

When a current test was performed on this device, a blue emission of 101 cd / m ² was obtained at a voltage of 6.4 V and a current density of 0.65 mA / cm ² , and the chromaticity coordinates were (0.1 7, 0.39), and the efficiency was 15.6 cd / A.

 Flrpic

Examples 5 and 6

 An organic EL device was prepared in the same manner as in Example 4 except that the compound shown in Table 2 was used instead of the compound (1), and the triplet energy and singlet energy, voltage, and current were similarly measured. Table 2 shows the measurement results of density, luminance, luminous efficiency, and chromaticity. Comparative Example 3

An organic EL device was prepared in the same manner as in Example 4 except that the above compound (BCz) was used instead of the compound (1), and a triplet energy and a singlet energy were similarly produced. Table 2 shows the measurement results of voltage, current density, luminance, luminous efficiency, and chromaticity. Comparative Example 4

 In Comparative Example 3, the compound (α-NPD) was used in place of the compound (TPAC) in the hole transport layer, and the compound (BA1) was used in place of the compound (Alq) in the electron injection layer. An organic EL device was fabricated in the same manner except that q) was used, and the triplet energy and singlet energy, voltage, current density, luminance, luminous efficiency, and chromaticity were measured in the same manner as shown in Table 2. Was.

As shown in Table 2, the organic EL device using the material for an organic EL device of the present invention was driven at a lower voltage and higher in efficiency than the conventionally known compound (BCz) of Comparative Examples 3 and 4. Blue light emission is obtained. Further, since the material for an organic EL device of the present invention has a wide energy gap, light-emitting molecules having a wide energy gap can be mixed into the light-emitting layer to emit light. Industrial applicability

 As described above in detail, the use of a material for an organic EL device comprising the compound represented by the general formula (1) of the present invention makes it possible to utilize luminescent light, achieve low voltage, and achieve luminous efficiency. A high organic electroluminescent device can be obtained. Therefore, the organic electroluminescent device of the present invention is extremely useful as a light source for various electronic devices.

Claims

The scope of the claims

1. A material for an organic electroluminescence device comprising a compound represented by the following general formula (1).

(Wherein, X, ～Kai ₈ each represent a carbon atom or a nitrogen atom, at least one is a nitrogen atom. If X, one of ~ chi ₈ is a carbon atom, bonded to carbon atoms and are R, to R ₈ represents a substituent. in this case, R, to R ₈ in which adjacent are joined may form a ring. X of one another either to X ₈ is When it is a nitrogen atom, 〜R ₈ bonded to the nitrogen atom each represents an unshared electron pair, and R ₉ represents a substituent.

2. R and -R ₉ are each —L or one L— Y

(L is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 2 carbon atoms. 0 linear or branched alkyl group, substituted or unsubstituted cycloalkyl group having 6 to 40 carbon atoms, substituted or unsubstituted amino group having 2 to 40 carbon atoms, substituted or unsubstituted carbon number of 1 to 40 40 straight-chain or branched alkoxy groups, halogen atoms, nitro groups, or substituted or unsubstituted arylene groups having 6 to 40 carbon atoms, substituted or unsubstituted divalent complexes having 2 to 40 carbon atoms Ring group, substituted or unsubstituted C 1 -C 20 Linear or branched alkylene group, substituted or unsubstituted cycloalkyl having 6 to 40 carbon atoms

Y is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 20 carbon atoms. Linear or branched alkyl group, substituted or unsubstituted cycloalkyl group having 6 to 40 carbon atoms, substituted or unsubstituted amino group having 2 to 40 carbon atoms, substituted or unsubstituted carbon number of 1 to 4 2. The material for an organic electroluminescent device according to claim 1, wherein the material is represented by 0 linear or branched alkoxy group, halogen atom or nitro group.

3. The material for an organic electroluminescence device according to claim 1, wherein 1 to 3 of X and X ₈ are nitrogen atoms and the remaining are carbon atoms.

4. X, among ～Kai _8, a chi ₃ and / or X ₆ is a nitrogen atom, an organic electroluminescence device material according to claim 1 remainder are carbon atom.

5. The material for an organic electroluminescent device according to claim 1, wherein at least one of R, to R ₈ is an S-carbolinyl group.

 6. The material for an organic electroluminescence device according to claim 2, wherein L and / or Y is an iS-carbolinyl group.

 7. The material for an organic electroluminescence device according to claim 1, wherein an energy gap of a triplet is 2.5 to 3.3 eV.

 8. The material for an organic electroluminescent device according to claim 1, wherein the singlet has an energy gap of 2.8 to 3.8 eV.

 9. An organic electroluminescence device in which one or more organic thin film layers are sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is the material for an organic electroluminescence device according to claim 1. An organic electroluminescence device containing:

10. An organic electroluminescent device in which one or more organic thin film layers are sandwiched between a cathode and an anode, wherein the light emitting layer is the organic light emitting device according to claim 1. An organic electroluminescent element containing a material for an electroluminescent element.

 11 1. In an organic electroluminescent device in which one or more organic thin film layers are sandwiched between a cathode and an anode, the electron transport layer and / or the electron injection layer

An organic electroluminescence device comprising the organic electroluminescence device material according to claim 1.

 12 2. In an organic electroluminescence device in which one or more organic thin film layers are sandwiched between a cathode and an anode, the hole transport layer and / or the hole injection layer

An organic electroluminescence device comprising the material for an organic electroluminescence device according to claim 1.

 13. The organic electroluminescent device according to any one of claims 9 to 12, wherein the material for an organic electroluminescent device is an organic host material.

14. The organic electroluminescent device according to claim 9, further comprising an inorganic compound layer between at least one electrode and the organic thin film layer.

 15. The organic electroluminescence device according to any one of claims 9 to 12, wherein the organic thin film layer contains a phosphorescent compound.

 16. The organic electroluminescence device according to any one of claims 9 to 12, which emits blue light.